Rhinebeck: Mighty All Righty

by Anne Pyburn and photographs by David Cunningham, July 27, 2011

Rhinebeck epitomizes a blend of comfort and class. It’s unsurprising that this corner of Dutchess County was chosen for Chelsea Clinton’s wedding, probably as a place where everyone would feel at home and have a lovely time. That same warm, well-bred welcome tinged with hip is available even to those who don’t arrive by limo, year round: The Rhinebeck vibes are what attracted the bold-face names, and not the other way around.


The Greatest Show Off Earth

The Old Rhinebeck Aerodrome has one of the world’s finest collections of flying pioneer, WWI, and Lindbergh era airplanes. Started by pilot, showman, and dreamer Cole Palen over a half century ago, it’s a unique airfield out in a cow pasture setting that’s a step-back in time where daredevil air shows, thrilling open-cockpit biplane rides, special events, and a modest but amazing little aviation museum can be enjoyed from mid-June to mid-October.


Classy & Sassy

The walkable and bustling center of town is a shopping destination unlike any other in the Hudson Valley, busy and friendly and genteel. A dozen different independent retailers, for example, offer clothing—from the lush boutique ambiance of places like Winter Sun Summer Moon and Workers and Dreamers to the comfortably updated old-school feel of the Rhinebeck Department Store. Along with its classics, Rhinebeck supports the independent Northern Dutchess Pharmacy, and Williams Lumber maintains a hardware store, big-box competition be damned. And there’s always room for newborn flights of fancy like Bumble and Hive, the nifty little “emporium for the soul” offering home goods and jewelry in a cunning courtyard setting.

But Rhinebeck doesn’t just have a downtown shopping district, it has Montgomery Row, a premiere commercial destination offering health services, shopping galore, and Gigi Trattoria, a four-star Mediterranean restaurant. The 2003 expansion that added another 27,000 square feet of shopping and dining was named “Best New Development in Dutchess County” by the Dutchess County Planning Federation.